Attorney O’Malley began his career with one of the leading insurance defense firms in Southeastern Massachusetts. He went on to join the legal department of Liberty Mutual Insurance Company, one of the largest insurance companies in the country, rising to the position of Senior Trial Counsel.

While at Liberty Mutual, he was chosen to be designated counsel for some of the largest companies in the United States, including well known package delivery, retail, fast food, construction, elevator, and manufacturing companies. Attorney O’Malley regularly defended million dollars lawsuits, and tried hundreds of jury trials, bench trials, and arbitrations. Attorney O’Malley also annually instructed other senior Liberty Mutual lawyers from throughout the country at a nationally recognized, week-long, advanced trial advocacy program.

Attorney O’Malley chaired the Massachusetts Bar Association's annual motor vehicle accident litigation seminar nine years. Attorney O’Malley has also been asked to speak at continuing legal education programs sponsored by the Massachusetts Bar Association, Massachusetts Academy of Trial Lawyers, and Association of General Contractors of Massachusetts.

In 2007, after 23 year of representing defendants in lawsuits, Attorney O’Malley left Liberty Mutual. While he continues to represent defendants in civil lawsuits, he now concentrates his practice in the representation of injured persons.

While Attorney O’Malley’s practice is based on the South Shore, he represents clients throughout Massachusetts from Hyannis to Springfield.